Orient's great years were in the 1960s and 1970s. In the 1961/62 season Orient were promoted to the top division of English football, the First Division (now the FA Premier League), for the only time in their history, after finishing second in Division Two under the management of Johnny Carey. The club struggled in the top flight and were relegated from the top division the next campaign. Nonetheless, they did beat West Ham United in a memorable 'double' victory (home and away wins). They spent the whole of the 1970s in the second division. In 1978 Orient were beaten in the last four of the FA Cup, the furthest they have progressed in that tournament.

Leyton Orient were Division Three South winners in the 1955/56 season and Division Three champions in the 1969/70 season. They were also the Anglo-Scottish Cup Runners up 1976/77.

In 1978 the team was indirectly responsible for the album Variations (album) written by Andrew Lloyd Webber for his brother, the cellist Julian Lloyd Webber. This reached No.2 in the pop album charts. Variations was as the result of a bet between the two siblings on the outcome of Orient's final match of the 1976/77 season facing Hull City.

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